Winchester, VA Homes

• 

  

  

  /23

  $452,990 New Construction

  • 2 - 3 Beds
  • 2 - 3 Baths
  • 1,564+ Sq Ft

  Hemingway Plan at Hiatt Pointe at Snowden Bridge - 55+ Garden Homes Collection, Winchester, VA 22603

  Welcome to your ideal one-level villa- the Hemingway! This thoughtfully designed home centers around a spacious kitchen, perfect for both daily life and entertaining guests. The main level offers two generous bedrooms, including a primary suite featuring a large walk-in closet and a private en suite bathroom for ultimate comfort. Convenience is key with a laundry room located just off the 2-car

  

  Brookfield Residential

  Builder

  105 Wagtail Ln Unit 36578850, Winchester, VA 22603
• 

  

  

  /25

  $1,645 - $2,477 per month

  Peppertree VA

  1 - 3 Beds

  221 Peppertree Ln, Winchester, VA 22601

  Tastefully designed 1, 2 and 3 bedroom floor plans and richly landscaped surroundings make for a welcome sight to call your home. Located in the heart of Winchester, Peppertree offers the conveniences of city living in a park-like setting. Peppertree is in close proximity to shopping, restaurants, schools and Winchester Medical Center.

  221 Peppertree Ln, Winchester, VA 22601
• 

  

  

  /47

  $550,000 Sold Sep 05, 2025

  • 2,203 Sq Ft
  • $250/SF
  • 81 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2019

  167 Morning Glory Dr, Winchester, VA 22602

  Welcome to the beautiful Twin Lakes Community! This charming ranch-style residence offers the ease of one-level living with a spacious and thoughtfully designed floor plan. The main level features a welcoming front den—perfect for a home office or reading nook—an updated kitchen with a large pantry area, a dining room filled with natural light, and a cozy family room complete with a gas

  Lisa Behr Coldwell Banker Premier

  167 Morning Glory Dr, Winchester, VA 22602
• 

  

  

  /11

  Est $129,582 Not Listed For Sale

  1137 Tomahawk Trail, Winchester, VA 22602

  1137 Tomahawk Trail, Winchester, VA 22602
• 

  

  /2

  $399,990 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,630 Sq Ft

  Bedford II Plan at Village at Valor Crossing - Townhomes, Winchester, VA 22601

  Covered front porch leads into the foyer. Attached 1 car garage or optional flex room or study. Open concept kitchen located next to the country kitchen and living room. Box bay rear window and 10' x 14' deck. Owner’s suite with large walk-in closet, dual vanity, and oversized seated shower in owner’s bath. Fireplace option available in select homes.

  

  DRB Homes

  Builder

  0 Tbd Weems Ln Unit 36470375, Winchester, VA 22601
• 

  

  /11

  $1,150 per month

  • 1 Bed
  • 1 Bath
  • 420 Sq Ft
  • Condo for Rent

  1704 Roberts St Unit 5, Winchester, VA 22601

  RECENTLY RENOVATED, ALL-BRICK BUILDING THAT WAS COMPLETELY REDONE OVER LAST SEVERAL YEARS * UNIT HAS NEWER STAINLESS-STEEL APPLIANCES AND NEWER VINYL-PLANK FLOORING * EXTERIOR OF BUILDING WAS PAINTED IN 2018. NEW WINDOWS, NEW GUTTERS AND NEW ROOF ADDED IN 2018. ALL NEW ELECTRIC SERVICE IN 0218, ALSO * AWESOME KITCHEN W/NEWER CABINETS & GRANITE C'TOPS * REDONE BATH W/CERAMIC TILE FLOORS & TUB

  John Gregory Holmes Samson Properties

  1704 Roberts St Unit 5, Winchester, VA 22601
• 

  

  /40

  $359,000 Sold Sep 05, 2025

  • 1,466 Sq Ft
  • $245/SF
  • 86 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1970

  124 Wilkins Dr, Winchester, VA 22602

  Welcome home to this newly remodeled and upgraded ranch style home. All the convenience of one level living, with the option of a basement full of possibilities. Step into the spacious living room, complete with fireplace, as you walk in the front door. Continue through the wonderful flow of the house into the dining room and open kitchen. Enjoy making your meals in the fully renovated kitchen

  Dave Spence RE/MAX Roots

  124 Wilkins Dr, Winchester, VA 22602
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  /7

  Est $101,377 Not Listed For Sale

  130 Lilac Ln, Winchester, VA 22602

  130 Lilac Ln, Winchester, VA 22602
• 

  

  /24

  $454,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,665 Sq Ft

  CABRAL Plan at Retreat at Winding Creek - Single Family, Winchester, VA 22602

  The Cabral, a 1,657 square foot open concept two-story home, offers three bedrooms, two and a half bathrooms, a loft and a two-car garage. As you make your way from the front porch into the foyer you will find a convenient first-floor powder room and coat closet. Past the foyer is the large, open concept living room that flows nicely into the eat-in kitchen that overlooks the casual dining area

  

  D.R. Horton

  Builder

  137 Seminole Dr Unit 36203778, Winchester, VA 22602
• 

  

  /25

  $1,605 per month

  HARRISON PLAZA RESIDENTIAL

  1 - 2 Beds

  2310 Valor Dr, Winchester, VA 22601

  Harrison Plaza is a new mixed-use development located at the intersection of Hope Drive and Valor Drive in the heart of Winchester, VA. This three-building community offers 70 one- and two-bedroom spacious modern apartments minutes away from local shopping centers, restaurants, and entertainment venues.Interior features include an open floor plan with stylish cabinets, granite countertops,

  2310 Valor Dr, Winchester, VA 22601
• 

  

  /36

  $490,000 Sold Sep 05, 2025

  • 2,296 Sq Ft
  • $213/SF
  • 124 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1997

  224 Lauck Dr, Winchester, VA 22603

  Custom Home in Historic Star Fort: Timeless Charm Meets modern Comfort for Discerning Buyers.This impeccably designed 3-bedroom, 2.5-bath home is a harmonious blend of classic elegance and contemporary convenience. Boasting cherry wood flooring throughout the main living areas, high-quality tile in the kitchen and bathrooms, and carpeted bedrooms, this home is as stylish as it is practical.

  Gidget Smallwood Coldwell Banker Premier

  224 Lauck Dr, Winchester, VA 22603
• 

  

  /30

  Not Listed For Sale

  301 Great Mountain Ln, Winchester, VA 22602

  301 Great Mountain Ln, Winchester, VA 22602
• 

  $452,539 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,630 Sq Ft

  0 Homesite 20 Monteith Dr Unit 36425637, Winchester, VA 22601

  End Of Row Townhome With 1 Car Garage, Gourmet Kitchen & Rear Deck! This home has a Gourmet Kitchen: cooktop with chimney style hood, wall microwave, wall oven, upgraded gourmet Energy Star stainless steel appliances, Refrigerator is a French 2 door style, the kitchen island is extended to comfortably seat 4, a box bay window in the rear of the home for extra lighting, and a 10 ft. x 14 ft. deck.

  

  DRB Homes

  Builder

  0 Homesite 20 Monteith Dr Unit 36425637, Winchester, VA 22601
• 

  

  /14

  $2,000 per month

  • 1 Bed
  • 1 Bath
  • 1,076 Sq Ft
  • Condo for Rent

  160 N Loudoun St Unit 202, Winchester, VA 22601

  Your dream of a modern apartment in Historical Winchester has finally arrived! Walk in to this one bedroom, one bathroom apartment and be instantly awed. The kitchen has everything you could need - including tons of cabinet space, granite countertops, a gas range, and a subtle backsplash that gives the room a sleek finish. Living room/dining room combo makes this space feel even bigger! Retire in

  Chris Roszko Colony Realty

  160 N Loudoun St Unit 202, Winchester, VA 22601
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  /78

  $1,200,000 Sold Sep 04, 2025

  • 5,117 Sq Ft
  • $235/SF
  • 11 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1992

  325 Windsor Ln, Winchester, VA 22602

  Welcome to 325 Windsor Ln, a stately brick Georgian-style home on 5 open and wooded acres in Winchester’s desirable Long Meadows community. This timeless residence offers privacy, serenity, and refined indoor-outdoor living just minutes from Winchester!Inside, the gourmet kitchen is a culinary showpiece featuring 36" custom cabinetry, granite countertops, two Sub-Zero refrigerators, a

  Sherry Pullen Samson Properties

  325 Windsor Ln, Winchester, VA 22602
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  /28

  Est $401,256 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,261 Sq Ft

  125 Cheshire Ct, Winchester, VA 22602

  125 Cheshire Ct, Winchester, VA 22602
• 

  $433,880 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,630 Sq Ft

  0 Homesite 117 Monteith Dr Unit 36422335, Winchester, VA 22601

  3 Level End of Row Townhome With 1 Car Garage & Rear Deck! Beautiful open concept living 3 level town home built on concrete slab with a walk-out lower level. Finished Rec Room - 13 ft. 1 in. x 11 ft. 1 in. with a door to the outside/backyard. The living room area is 15 ft. 3 in. x 17 ft., open kitchen layout with an extended island, a box bay window and 10 ft. x 14 ft. deck in the rear of home.

  

  DRB Homes

  Builder

  0 Homesite 117 Monteith Dr Unit 36422335, Winchester, VA 22601
• 

  

  /25

  $1,400 - $2,010 per month

  PEMBERTON

  2 - 3 Beds

  660 Pemberton Dr, Winchester, VA 22601

  Pemberton Village Apartments in Winchester VA is located in the prestigious Meadow Branch subdivision near the intersection of Jubal Early Drive and Harvest Drive. It is a ten building, 120 unit community easily assessable from Interstate 81 or Route 37. Conveniently located near the Apple Blossom Mall, fitness centers, John Handley High School, and Valley Health Medical Center; Pemberton Village

  660 Pemberton Dr, Winchester, VA 22601
• 

  

  /39

  $408,000 Sold Sep 04, 2025

  • 1,664 Sq Ft
  • $245/SF
  • 6 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1993

  100 Lloyds Rd, Winchester, VA 22602

  Charming 4 BD/2BA Cape Cod in Carlisle Heights - Corner Lot with Private Backyard! Welcome to this well-maintained Cape Cod home in the desirable Carlisle Heights neighborhood. Featuring 4 bedrooms and 2 full baths, this home is set on a spacious corner lot with a fenced backyard, patio, and storage shed-perfect for relaxing or entertaining. Inside you will find hardwood floors, a wood-burning

  Christine Liggett Samson Properties

  100 Lloyds Rd, Winchester, VA 22602
• 

  

  /4

  Est $1,341,995 Not Listed For Sale

  601 W Jubal Early Dr, Winchester, VA 22601

  601 W Jubal Early Dr, Winchester, VA 22601
• 

  $429,340 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,630 Sq Ft

  0 Homesite 114 Monteith Dr Unit 36422292, Winchester, VA 22601

  3 Level Townhome With Over 1,600 Finished sq. ft., 1 Car Garage & Rear Deck! Bedford II, 3 level townhome features a partial stone front with 1 car garage. This home features 3 Bedrooms and 3.5 Baths. It is fully finished top to bottom. The front door leads directly into the spacious lower level including 9 ft. ceilings, foyer with a double coat closet, access to the garage with a garage door

  

  DRB Homes

  Builder

  0 Homesite 114 Monteith Dr Unit 36422292, Winchester, VA 22601
• 

  

  /22

  $1,250 per month

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft
  • Condo for Rent

  540 Monticello St Unit 1, Winchester, VA 22601

  Discover this cozy and convenient 2-bedroom, 1-bath rental located right in the heart of Winchester. Featuring a well-sized kitchen, comfortable living room, and the convenience of in-unit laundry, this home makes everyday living easy.-2 Bedrooms, 1 Full Bath-Spacious kitchen + small living room-In-unit laundry-Great city location with easy access to shopping, dining, and

  Laura King MarketPlace REALTY

  540 Monticello St Unit 1, Winchester, VA 22601
• 

  

  /79

  $638,750 Sold Sep 04, 2025

  • 2,833 Sq Ft
  • $225/SF
  • 34 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2000

  283 Huntersridge Rd, Winchester, VA 22602

  Price improvement!!!The One You've Been Waiting For: 283 Huntersridge Rd – Luxury, Space, Pool & NO HOA!Stop your search! Tucked away in sought-after Oakdale Crossing, this remarkable 4-bedroom, 2.5-bathroom Colonial delivers pure luxury – all without the burden of an HOA! This isn't just a house; it's the home you've been dreaming of, packed with features that defy its price

  George Hockaday-Bey All Service Real Estate

  283 Huntersridge Rd, Winchester, VA 22602
• 

  

  /6

  Est $172,220 Not Listed For Sale

  106 Mate Ct, Winchester, VA 22602

  106 Mate Ct, Winchester, VA 22602
• 

  

  /44

  $782,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 6,122 Sq Ft

  939 Buckner Dr, Winchester, VA 22601

  Priced to se!!! Listed well below market value, this stunning all-brick home in the sought-after Meadow Branch community was built in 2000 and has undergone extensive renovations in 2023 and 2024. The main-level bedroom includes a spacious, newly updated ensuite featuring an oversized marble-tiled shower, dual vanities, and a custom walk-in closet designed by ClosetsByDesign. The beautifully

  Kiran K. Morzaria Parekh Redfin Corporation

  939 Buckner Dr, Winchester, VA 22601
• 

  

  /25

  $1,600 - $2,600 per month

  Apartment for Rent

  Studio - 2 Beds

  114 N Loudoun St, Winchester, VA 22601

  Brand new fully furnished extended stay apartments in the heart of Old Town Winchester Virginia including all utilities, washer /dyer, high speed internet, free nightly and weekend parking ( 5pm to 8 am), keyless entry, 10' ceilings, exposed brick interior partitions and optional weekly cleaning.. More information can be found at themerchantsuites

  114 N Loudoun St, Winchester, VA 22601
• 

  

  /30

  $380,000 Sold Sep 04, 2025

  • 1,431 Sq Ft
  • $266/SF
  • 31 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2004

  1826 Kershaw Ln, Winchester, VA 22601

  This charming one-level home is perfectly situated in one of Winchester's desirable 55+ senior communities, Willow Lawn Cottages. Great home....first time on the market,featuring two spacious bedrooms, two full bathrooms, hardwood floors & vaulted ceilings. The open and inviting floor plan will make your new home ideal for both daily living and entertaining. The large primary suite offers

  Jeff Webber Long & Foster Real Estate, Inc.

  1826 Kershaw Ln, Winchester, VA 22601
• 

  

  /12

  Not Listed For Sale

  • Studio
  • 2,376 Sq Ft

  1021 Franklin St, Winchester, VA 22601

  1021 Franklin St, Winchester, VA 22601
• 

  

  /39

  $513,579 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,181 Sq Ft

  115 Wagtail Ln, Winchester, VA 22603

  Embrace the Vera 30-F2 – Homesite 1030 at Hiatt Pointe—a two-car, front-load garage END UNIT VILLA with three bedrooms, two full bathrooms, and one half bathroom is ready for move-in IMMEDIATELY. Built for the way you live, this factory-framed floorplan makes room for moments big and small. Be welcomed by 9’ ceilings on both levels, oak main stairs, and expertly selected finishes that make this

  Shannon L Bray Pearson Smith Realty, LLC

  115 Wagtail Ln, Winchester, VA 22603
• 

  

  /19

  $1,400 per month

  • 2 Beds
  • 1 Bath
  • 8,508 Sq Ft
  • Condo for Rent

  113 W Boscawen St Unit 3, Winchester, VA 22601

  3rd floor walk-up apartment. In the middle of downtown Winchester is this 2 bedroom, 1 bath apartment featuring an abundancy of light with numerous windows, large rooms and hardwood floors. Primary bedroom has direct access to bathroom. Water, sewer and trash pick-up is provided in the monthly rent as is 1 parking space in the Braddock Street Parking Garage. Tenant is responsible for

  Barbara Gaul Jim Barb Realty, Inc.

  113 W Boscawen St Unit 3, Winchester, VA 22601
• 

  

  /71

  $779,000 Sold Sep 04, 2025

  • 1,456 Sq Ft
  • $535/SF
  • 110 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2002

  251 Heather Hill Ln, Winchester, VA 22603

  Back on market at NO fault of seller. Have you been looking for peace and serenity, then you've found it. This gorgeous property offers almost 50 acres (there are several different parcels included in this sale. Parcels that are included are: 19-3-7 (house parcel, 5 acres), 19-3-10 (garage, pole barn parcel, 5 acres), 19-3-12 (7.79 acres), 19-A-48 (31.04 acres). The lovely Chalet offers 3

  Amber Jenkins Century 21 Redwood Realty

  251 Heather Hill Ln, Winchester, VA 22603
• 

  

  /62

  Est $724,805 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 4,422 Sq Ft

  231 Summerfield Dr, Winchester, VA 22602

  231 Summerfield Dr, Winchester, VA 22602
• 

  

  /53

  $774,499 Pending

  • 5 Beds
  • 3.5 Baths
  • 3,928 Sq Ft

  977 W Parkins Mill Rd, Winchester, VA 22602

  Welcome to your dream retreat—set on 5 private acres just outside Winchester, this fully renovated home offers the perfect blend of luxury and land. With 5 spacious bedrooms and 3.5 beautifully updated bathrooms, this property is designed for comfort, functionality, and style.From the chef’s kitchen to the expansive living areas, every detail has been thoughtfully upgraded. Whether you're

  Nicole Renzetti EXP Realty, LLC

  977 W Parkins Mill Rd, Winchester, VA 22602
• 

  

  /25

  $1,750 per month

  CEDAR HILL APARTMENTS

  2 - 3 Beds

  2250 Sofia Way, Winchester, VA 22601

  Cedar Hill Apartments offers well-appointed accommodations located in a convenient and relaxing environment. Only minutes away from Route 37, Route 11, and Jubal Early Drive, Cedar Hill apartments offers its tenants easy access to the Winchester Medical Center, Shenandoah University, loads of shopping and restaurants. Interior features include vaulted ceilings, gas fireplace, wood vanity

  2250 Sofia Way, Winchester, VA 22601
• 

  

  /55

  $305,000 Sold Sep 03, 2025

  • 2,188 Sq Ft
  • $139/SF
  • 5 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 2003

  104 Seabreeze Ln, Winchester, VA 22602

  Welcome home to this 3-bedroom, 1.5-bath townhome offering comfort, space, and convenience—just minutes from Rt 7 and I-81, perfect for commuters. This well-maintained home features vinyl siding and a welcoming traditional floor plan. The spacious living room boasts a modern gray accent wall and flows seamlessly into the open kitchen and dining area. Enjoy cooking and entertaining with a kitchen

  Tana Hoffman Sager Real Estate

  104 Seabreeze Ln, Winchester, VA 22602
• 

  

  /41

  Est $467,682 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,776 Sq Ft

  2060 Taylor Grace Ct, Winchester, VA 22601

  2060 Taylor Grace Ct, Winchester, VA 22601
• 

  

  /39

  $556,249 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,279 Sq Ft

  104 Wagtail Ln, Winchester, VA 22603

  Welcome to the Vale 34-F2 – Homesite 1023 at Hiatt Pointe—a two-car, front-load garage END VILLA with three bedrooms, two full bathrooms, and one half bathroom will be ready IMMEDIATELY. Open and adaptable, this factory-framed floorplan blends functionality with comfort. Enter through the welcoming front porch and be immediately greeted by 9’ ceilings on both levels, oak main stairs, and expertly

  Shannon L Bray Pearson Smith Realty, LLC

  104 Wagtail Ln, Winchester, VA 22603
• 

  

  /11

  $1,500 per month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Townhouse for Rent

  112 Waterford Ln, Winchester, VA 22602

  Great location - near I-81, Rt. 7 & 50. Living room with recently refinished hardwood floors, updated kitchen - counters and appliances; updated windows. 2 bedrooms and 1 bath. Washer/dryer in unit. Fenced backyard with storage closet. 2 assigned parking spaces. No pets or smoking.

  Barbara Gaul Jim Barb Realty, Inc.

  112 Waterford Ln, Winchester, VA 22602
• 

  

  /40

  $330,000 Sold Sep 03, 2025

  • 1,008 Sq Ft
  • $327/SF
  • 3 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1980

  102 Maloy Dr, Winchester, VA 22602

  **** MULTIPLE OFFERS RECEIVED, DEADLINE FOR ALL OFFERS 8/4 AT 5PM *****Charming One-Level Rancher on Nearly an Acre in a Park-Like Setting WITH NO HOA! Meticulously maintained and brimming with character, this delightful 2-bedroom, 2-bathroom ranch-style cottage sits on a beautifully flat, nearly one-acre lot on the desirable east side of Winchester. Thoughtfully updated with ADA-accessible

  Lisa Cox Colony Realty

  102 Maloy Dr, Winchester, VA 22602
• 

  

  /43

  Est $578,370 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,568 Sq Ft

  2044 Taylor Grace Ct, Winchester, VA 22601

  2044 Taylor Grace Ct, Winchester, VA 22601

Showing Results 121 - 160, Page 4 of 18